1. Field of the Invention
This invention relates to phosphoric esters of polyfluorinated alcohols, the derivatives thereof and their preparation.
2. Description of the Prior Art
Polyfluorinated phosphorus chain compounds are in great demand. Those which are polar enough, particularly those which are terminated by the acid group PO.sub.3 H.sub.2, eventually neutralized, are appreciated for their surface properties and for the hydrophobic and oleophobic properties they impart to textiles, plastics, leather, waxes and the like. They are used as emulsifying agents in emulsion polymerization of fluorinated olefins (U.S. Pat. Nos. 2,559,754 and 2,676,985), as leveling and anti-stain agents for wax-polishes and emulsion brightening agents (U.S. Pat. No. 3,083,224 and French Pat. No. 1,454,535), or as additives for chromium plating baths (U.S. Pat. No. 3,194,840). Known compounds of this family are illustrated by phosphonic acids of formula C.sub.n F.sub.2n.sub.+1 (--CH.sub.2).sub.m --PO.sub.3 H.sub.2 (French Pat. No. 1,454,535) or formula H-- C.sub.n F.sub.2n -- PO.sub.3 H.sub.2 (U.S. Pat. No. 2,559,754), and by partial phosphoric esters of the formula [C.sub.n F.sub.2n.sub.+1 (CH.sub.2).sub.m O].sub.p PO (OH).sub.3.sub.-p (U.S. Pat. No. 3,083,224), at least one of these compounds being sold under the name of ZONYL S 13, the latter being a trademark of Du Pont de Nemours.
Other phosphorus compounds having a polyfluorinated chain are used as lubricating agents or additives therefore; for example, neutral phosphoric esters having the formula (C.sub.n F.sub.2n.sub.+1 --CH.sub.2 O).sub.3 PO (U.S. Pat. No. 2,888,481), esters of polyfluorinated phosphonic acids such as H (CF.sub.2).sub.n (CH.sub.2).sub.3 -- PO (OCH.sub.3).sub.2 (French Pat. No. 1,454,535) and esters of polyfluorinated alcohols of benzene phosphonic acid (U.S. Pat. No. 3,337,665).
Similar compounds are used as hydraulic fluids: for example, phosphoric esters of polyfluorinated alcohols (U.S. Pat. Nos. 2,754,317 and 2,754,318), phosphonic esters of polyfluorinated alcohols (U.S. Pat. No. 3,246,030) or of polyfluoroalkylphenols (French Pat. No. 1,430,849), phosphoramidates of polyfluorinated alcohols (French Pat. No. 1,450,918) or esters of N - polyfluoroalkyl phosphoramidic acids (Belgian Pat. No. 672,659).